The Keep with Next setting cascades. This means that if the preceding element also has Keep with Next turned on and the one before it, and the one before it then they all 'try' to keep with next until they run out of space at the bottom of the page.

In your first picture you have a table followed by an empty paragraph and then the heading. The empty paragraph has the Keep with Next turned on as evidenced by the small black square that kind of looks like a bullet. Tables can be tricky because if the first paragraph in the table has "keep with next" turned on, the entire table can behave that way. In my opinion that behaviour is a bug and its been a problem for the last few versions of Word.

So the solution for you is to either:
- select the table and turn off Keep with Next OR
- put a small empty paragraph between the table and the heading and make sure that paragraph does not have Keep with Next turned on. I use a style called 'Spacer' for this purpose.

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Andrew Lockton
Chrysalis Design, Melbourne Australia